2,6-Di-tert-butyl-4-methylphenol is a known antioxidant. Various methods are available for its production.
U.S. Pat. No. 2,841,624 describes a process whereby 2,6-di-tert-butyl-4-methylphenol can be produced by reacting 3,5-di-tert-butyl-4-hydroxybenzyl alcohol or ether in the presence of an alcohol and a base.
U.S. Pat. No. 3,006,969 teaches the catalytic hydrogenation of 3,5-di-tert-butyl-4-hydroxybenzyl methyl ether to obtain 2,6-di-tert-butyl-4-methylphenol.
U.S. Pat. No. 3,030,428 indicates that 2,6-di-tert-butyl-4-methylphenol can be made by reacting 3,5-di-tert-butyl-4-hydroxybenzyl alcohol with hydrogen in the presence of a catalyst.
U.S. Pat. No. 4,117,244 teaches the production of 2,6-di-tert-butyl-4-methylphenol by the catalytic hydrogenation of N,N-dimethyl-3,5-di-tert-butyl-4-hydroxybenzyl amine.
A halomethyl group substituted on an aromatic compound may be converted to a methyl group by a variety of known chemical reducing agents. The article "9-BBN Ate Complexes As A New Type Of Reducing Agent For The Selective Reduction Of Tertiary Alkyl, Benzyl, And Allyl Halides To Hydrocarbons" in J. Am. Chem. Soc., (1975) 97:9, pages 2558-9, discusses the selective removal of a number of types of halides to afford the corresponding hydrocarbons in excellent yields without concomitant attack on secondary, primary and aryl derivatives. Several substrates were reduced including benzyl chloride to toluene and diphenylchloromethane to diphenylmethane.
"Organic Reactions," Volume VII, Chapter 5, pages 263 through 326 discusses the hydrogenolysis of benzyl groups attached to oxygen, nitrogen and sulfur using a palladium catalyst to obtain a methyl group substituted on an aromatic ring. The technique whereby a halomethyl group attached to an aromatic ring is converted to a methyl group is not considered.